alpha-cyclopropylbenzylurea



United States Patent F 3,000,938 a-CYCLOPROPYLBENZYLUREA Warren J.Close, Waukegan, Ill., assignor to Abbott Laboratories, North Chicago,111., a corporation of Illinois No Drawing. Original application Oct. 9,19'56, Ser. No. 614,803. Divided and this application Oct. 22, 1959,Ser. No. 16,908

1 Claim. (Cl. 260-553) HaOH III wherein Ar represents an aromatichydrocarbon and H is a hydrogen atom in the nucleus of the aromatichydrocarbon. The cyclopropyl aryl ketone III is obtained by treating IIwith potassium hydroxide and methanol. Novel derivatives of thecyclopropyl aryl ketone III exhibit definite activity as anticonvulsantsand hypnotics. These compounds have the formula -CH-Ar it the scope ofthe appended claim.

Patented Sept. 19, 1961 2 wherein Ar is a Friedel-Orafts reactingaromatic group and R is ureido.

Using cyclopropyl phenyl hetone as a starting material, it is possibleto prepare related compounds by substitutions of the ketone group. Thefollowing example illustrates illustrates the preparation of such aderivative, but it should be understood that such preparation does notexclude the possible use of cyclopropyl ary-l ketones other thancyclopropyl phenyl ketone as a starting material. The aromatic moiety ofthe cyclopropyl aryl ketone can be any aromatic compound which undergoesa Friedel- Crafts reaction to form said cyclopropyl aryl ketones in themanner heretofore disclosed, such as toluene, chlorobenzene, phenetole,naphthalene, thiophene, benzothiophene and the like as disclosed in saidcopending application.

EXAMPLE u-Cyclopropylbenzylurea 9.2 grams (0.05 mole) ofa-cyclopropylbenzylamine hydrochloride is dissolved in cc.of water andtreated with 4.9 grams (0.06 mole) of potassium cyanate in 20 cc. ofwater. The mixture is allowed to stand for several hours after which theformed product, u-cyclopropylbenzylurea, is separated by filtration in ayield of 8.0 grams having a melting point of 143-146 C.

Analysis.0alcd. for C H N N, 14.7. Found: N, 14.9. 1

Others may practice the invention in any of the numerous Ways which willbe suggested by this disclosure to one skilled in the art. All suchpractice of the invention is considered to be a part hereof provided itfalls I claim: The compound a-cyclopropylbenzylurea.

References Cited in the file of this patent Close: J. Am. Chem. Soc,vol. 79, pages 1455-8 (1957).

